Collective Total Synthesis of Aspidofractinine Alkaloids through the Development of a Bischler–Napieralski/Semipinacol Rearrangement Reaction
Shuang‐Hu Wang, Rui‐Qi Si, Qing‐Bo Zhuang, Xiang Guo, Tian Ke, Xiaoming Zhang, Fu‐Min Zhang, Yong‐Qiang Tu
Abstract
A tandem Bischler-Napieralski/semipinacol rearrangement reaction has been developed for the purpose of assembling a bis(spirocyclic) indole framework, a privileged structural unit of aspidofractinine-type monoterpenoid indole alkaloids, and was used in combination with a subsequent Mannich reaction to expeditiously construct the central bridged bicyclo[2.2.1]heptane ring system of these molecules with contiguous quaternary centers. The development of this novel strategy culminated in the collective total synthesis of four aspidofractinine alkaloids.
Topics & Concepts
ChemistryHeptaneRing (chemistry)StereochemistryMannich reactionIndole testTotal synthesisTandemOrganic chemistryMaterials scienceCatalysisComposite materialAlkaloids: synthesis and pharmacologyPlant-based Medicinal ResearchTraditional and Medicinal Uses of Annonaceae